The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

Mark T. Blankenbuehler; John P. Selegue

doi:10.1016/S0022-328X(01)01185-8

The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

Mark T. Blankenbuehler, John P. Selegue

Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or Bu^tCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.

Original language	English
Pages (from-to)	268-274
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	642
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(01)01185-8
State	Published - 2002

Bibliographical note

Funding Information:
We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.

Keywords

Acyl
Carboethoxy
Cyclopentadienide
Formyl
Thallium
Vilsmeier

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(01)01185-8

Cite this

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title = "The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds",

abstract = "The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or ButCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.",

keywords = "Acyl, Carboethoxy, Cyclopentadienide, Formyl, Thallium, Vilsmeier",

author = "Blankenbuehler, {Mark T.} and Selegue, {John P.}",

note = "Funding Information: We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.",

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doi = "10.1016/S0022-328X(01)01185-8",

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T1 - The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

AU - Blankenbuehler, Mark T.

AU - Selegue, John P.

N1 - Funding Information: We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.

PY - 2002

Y1 - 2002

N2 - The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or ButCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.

AB - The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or ButCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.

KW - Acyl

KW - Carboethoxy

KW - Cyclopentadienide

KW - Formyl

KW - Thallium

KW - Vilsmeier

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EP - 274

IS - 1-2

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The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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